(3-oxobutyl)diphenylphosphine oxide | 67217-31-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-oxobutyl)diphenylphosphine oxide
• 英文别名: 3-oxobutyl-diphenylphosphine oxide；1-(Diphenylphosphinyl)butan-3-one；4-(diphenylphosphinyl)-2-butanone；4-(diphenylphosphinyl)butan-2-one；4-(diphenylphosphoryl)butan-2-one；4-diphenylphosphorylbutan-2-one
• CAS: 67217-31-6
• 化学式: C₁₆H₁₇O₂P
• 分子量: 272.284
• InChiKey: FGRDRRNGJCVNAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-oxobutyl)diphenylphosphine oxide 在 盐酸 、 sodium hydroxide 、 N-氯代丁二酰亚胺 、 正丁基锂 、 二甲基硫 、 四甲基乙二胺 、 三乙胺 、 mercury dichloride 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 甲苯 、 苯 为溶剂， 反应 9.27h， 生成 5-(Diphenylphosphinyl)-2,3-dimethylcyclopent-2-en-1-one
  参考文献：
  名称：

  Methylenomycin B: new syntheses based on .beta.- and .gamma.-keto phosphonates and .gamma.-keto phosphine oxides

  摘要：

  Methylenomycin B has been synthesized from diethyl 2-oxobutanephosphonate (4) in three steps in 39% overall yield. Starting from diethyl 3-oxobutanephosphonate (10) and diphenyl(3-oxobutyl)phosphine oxide (13), methylenomycin B has been obtained in 34% and 27% overall yield, respectively. A characteristic feature of these syntheses of methylenomycin B is that the exo-methylene function is introduced via the Horner-Wittig reaction of formaldehyde (36% aqueous solution) with the corresponding alpha-phosphorylcyclopentenones 6 and 20. The latter were obtained from phosphorylated 1,4-diketones by intramolecular base-catalyzed cyclization. A brief discussion of some mechanistic aspects of the Conant reaction is also given.

  DOI：

  10.1021/jo00003a051
• 作为产物：
  描述：

  [2-(2-Methyl-1,3-dithian-2-yl)ethyl](triphenyl)phosphanium bromide 在 sodium hydroxide 、 ammonium cerium(IV) nitrate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 48.0h， 生成 (3-oxobutyl)diphenylphosphine oxide
  参考文献：
  名称：

  Oxidative hydrolysis of .gamma.-thioacetalated phosphonium salts. Influence of the counterion on the course of the reaction

  摘要：

  DOI：

  10.1021/jo00185a041

文献信息

• Me 3 P-catalyzed addition of hydrogen phosphoryl compounds P(O)H to electron-deficient alkenes: 1 to 1 vs 1 to 2 adducts
  作者：Tian-Zeng Huang、Tieqiao Chen、Yuta Saga、Li-Biao Han

  DOI：10.1016/j.tet.2017.10.070

  日期：2017.12

  Trimethyl phosphine was used as an efficient catalyst for the addition of P(O)-H compounds to electron-deficient alkenes. The addition reactions were generally conducted using a catalytic amount of Me3P under mild reaction conditions. Both 1 to 1 and 1 to 2 adducts were obtained.

  三甲基膦被用作将P（O）-H化合物加成至缺电子烯烃的有效催化剂。通常在温和的反应条件下使用催化量的Me 3 P进行加成反应。获得了1对1和1对2个加合物。
• α- and β-diphenylphosphorylated secondary alkanols: I. general method of synthesis and extraction properties towards f-elements
  作者：E. I. Goryunov、A. G. Matveeva、A. M. Safiulina、I. B. Goryunova、G. V. Bodrin、V. K. Brel

  DOI：10.1134/s1070363216030208

  日期：2016.3

  A simple and effective general method of synthesis of α- and β-diphenylphosphorylated secondary alkanols by the reduction of the corresponding phosphorylalkanones with NaBH4 was developed. The extraction properties of the resulting phosphorylalkanols Ph2P(O)(CR2)nCH2CH(OH)Me (n = 0, 1; R = H, Me) were studied in the recovery of f-elements (LaIII, NdIII, HoIII, YbIII, UVI, ThIV) from nitric acid solutions

  开发了一种简单有效的通用方法，该方法通过用NaBH4还原相应的磷酰基链烷酮来合成α-和β-二苯基磷酸化的仲链烷醇。研究了所得磷酰基链烷醇Ph 2 P（O）（CR 2）n CH 2 CH（OH）Me（n = 0，1; R = H，Me）的萃取特性，回收了f元素（La III），Nd III，Ho III，Yb III，U VI，Th IV）从硝酸溶液转化为氯仿，并与相关磷酮和已知萃取剂（n-BuO）3 PO，（n -C 8 H 17）3 PO和Ph 2 P（O）CH 2 C（O）N（n -Bu）2。
• New type of 2-alkyl-substituted 1,8-naphthyridine systems containing a phosphoryl group in the side chain
  作者：P. S. Lemport、G. V. Bodrin、M. P. Pasechnik、A. G. Matveeva、P. V. Petrovskii、A. V. Vologzhanina、E. E. Nifant’ev

  DOI：10.1007/s11172-007-0293-8

  日期：2007.9

  First organophosphorus derivatives of 2-alkyl-and 2,3-alkylene-substituted 1,8-naphthyridines were synthesized by the Friedländer reaction starting from 2-aminonicotinaldehyde and diphenylphosphoryl(cyclo)alkanones, respectively.

  首次通过Friedländer反应，分别以2-氨基烟醛和二苯基磷酰基(环)烷酮为原料，合成了2-烷基和2,3-亚烷基取代的1,8-萘啶的第一批有机磷衍生物。
• A study on the michael addition of dialkylphosphites to methylvinylketone
  作者：György Keglevich、Melinda Sipos、Daniella Takács、István Greiner

  DOI：10.1002/hc.20266

  日期：2007.4

  The addition of dialkylphosphites to methylvinylketone giving dialkyl-3-oxobutylphos- phonates was studied applying different reagents, such as NaOR/ROH, NaOH/H2O under PTC, DBU, and R3Al (R = Me, Et) under different conditions to find the optimum choice regarding efficiency and selectivity. Possible extensions to a few other model compounds were also investigated. © 2007 Wiley Periodicals, Inc. Heteroatom

  使用不同的试剂，如 NaOR/ROH、NaOH/H2O 在 PTC、DBU 和 R3Al（R = Me、Et）下，在不同条件下研究了将二烷基亚磷酸酯添加到甲基乙烯基酮中得到二烷基-3-氧代丁基膦酸酯以找到最佳关于效率和选择性的选择。还研究了一些其他模型化合物的可能扩展。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:226–229, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20266
• Friedländer reaction in the synthesis of 2-(phosphoryl)alkyl-substituted 1,6-naphthyridines
  作者：Pavel S. Lemport、Georgy V. Bodrin、Andrey I. Belyakov、Pavel V. Petrovskii、Anna V. Vologzhanina、Edward E. Nifant’ev

  DOI：10.1016/j.mencom.2009.11.002

  日期：2009.11

  First 2-(phosphoryl)alkyl-substituted 1,6-naphthyridines have been synthesized by the Friedlander reaction between 4-amino-3-formylpyridine and phosphorus-containing ketones; their structures have been confirmed by 1H, 13C and 31P NMR spectroscopy and X-ray diffraction analysis.

  通过2-氨基-3-甲酰基吡啶和含磷酮之间的弗里德兰德反应合成了第一个2-（磷酰基）烷基取代的1，6-萘啶；它们的结构已通过1H，13C和31P NMR光谱法以及X射线衍射分析证实。